Hydrochloric Acid → N-(4-methoxybenzoyl)-phenylalanyltyrosine

HRID 839938Notes

Reaction equation

HRID 839938 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:30]([O:32]C)=[O:31])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:30]([OH:32])=[O:31])[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=2)=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53971131methyl N-(4-methoxybenzoyl)phenylalanyltyrosinate

Product 1

HCID 54084741N-(4-methoxybenzoyl)-phenylalanyltyrosineYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In 150 ml of methanol, was dissolved 30 g of methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate. After addition of 145 ml of 1 N sodium hydroxide, the mixture was stirred at 50° C for 2 hours. The reaction mixture was neutralized with hydrochloric acid, concentrated and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 23.9 g of N-(4-methoxybenzoyl)-phenylalanyltyrosine with a mp. 198°-200° C in a yield of 82%. Analysis, calculated for C26H26O6N2C 67.52, H 5.67, N 6.06, found C 67.17, H 5.69, N 5.95.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-0dae20bacc3e4ea4967b311ffce4a3f6
Source dataset
uspto-grants-1978_06
Patent number
US04097608

Reaction notes

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